Hi there. This might not be best suited toward our forum, as the questions you're seeking to answer seem more geared to the psychology of artists and their process, rather than any specific historical detail about them. Plus as I'm sure you can see by our flaired users list, we are woefully short on music historians, who probably won't be Louis Armstrong specialists, although you might try contacting them directly to see what they know.

As such, this question (especially ones regarding psychology and philosophy) might be better suited to one of the other forums, like /r/asksocialscience, /r/askphilosophy or possibly even /r/jazz in order to get the information you need regarding Louis Armstrong's approach and understanding of music.